By Coshandra Dillard
Coshandra writes for Sandcastle Realty, sharing travel tips and the best things to discover on Martha's Vineyard to help guests plan memorable vacations.
Choosing where to stay in Martha’s Vineyard can feel overwhelming with so many locations and vacation rentals to consider. Whether you’re planning a solo escape, romantic getaway, trip with friends, family vacation, or larger group gathering, Sandcastle Realty offers accommodations for a variety of travel styles and budgets.
From simple, comfortable cottages to spacious homes and upscale retreats, Sandcastle Realty offers more than 250 vacation rentals across Martha’s Vineyard. On our site, you can narrow your search based on location, group size, dates, and amenities to find a home that fits your plans.
Our Edgartown-based team has helped visitors find Martha’s Vineyard rentals for more than 25 years. And when you book directly with us, you get the best price every time, without the additional fees charged by online travel agencies. It’s as simple as exploring and choosing. Then, you’re one step closer to a memorable escape to Martha’s Vineyard!
SEE ALL MARTHA'S VINEYARD VACATION RENTAL HOMES
In This Article:
- Rental Options That Fit Your Trip
- Where to Stay in Martha’s Vineyard by Location
- Book Your Martha’s Vineyard Rental Today!
- Frequently Asked Questions
Rental Options That Fit Your Trip
Martha’s Vineyard isn’t one-size-fits-all, and neither are our homes. Start with your must-haves. How many bedrooms do you need? Is a water view important? Do you want to walk to town, bring your pet, stay near the beach, or retreat somewhere quieter?
A smaller cottage can make a comfortable home base for a solo traveler or couple planning to spend much of the day exploring. It’ll give you everything you need if you plan to spend most of your time sightseeing, dining out, or enjoying the beach. If you’re traveling with your friends, you might prioritize multiple bedrooms and gathering space. If you’re traveling with a larger group, you’ll probably want additional living areas, a pool, or plenty of outdoor space.
Knowing your priorities can quickly narrow your choices and help you find a rental that complements how you want to experience the Island.
Where to Stay in Martha’s Vineyard by Location
It’s all about the location. Martha’s Vineyard offers everything from lively port communities to peaceful up-Island settings, and each provides a different vacation experience. We’ve highlighted several Martha’s Vineyard locations, featuring vacation rentals you can find through Sandcastle Realty.
Edgartown/Katama
Edgartown combines historic New England character with convenient access to restaurants, shops, beaches, and the waterfront. Head toward Katama for a more relaxed setting with easy access to South Beach.
Featured Property: 1833 Edgartown-Katama
2 Bedrooms | 1 Bathroom | Sleeps 4
This cozy one-story Katama cottage sits about a mile from South Beach, with the bike path right outside the door. A sunny sitting room, a back deck with outdoor dining, a gas grill, and an outdoor shower make it a comfortable choice when you want a smaller place with easy access to the beach and town.
Chappaquiddick
Just across the harbor from downtown Edgartown, Chappaquiddick offers a quieter setting surrounded by natural beauty. It’s a good choice if you want privacy and easy access to outdoor activities.
Featured Property 1948 Chappaquiddick
3 Bedrooms | 2 Bathrooms | Sleeps 6
Surrounded by trees on a quiet, private road, this renovated Chappaquiddick home combines a contemporary interior with ample outdoor living space. A screened porch, open-air deck, outdoor shower, and proximity to the Chappy Ferry, trails, and water make it especially appealing for an outdoors-focused getaway.
Oak Bluffs
Oak Bluffs combines its famous gingerbread cottages with a bustling harbor, restaurants, shops, and plenty of summer activity. Consider staying here if being close to town and having plenty to do nearby are high on your vacation wish list.
Featured Property: 1661 Oak Bluffs
4 Bedrooms | 3 Bathrooms | Sleeps 8
This four-bedroom cottage in the Sunset Lake area offers multiple living spaces, a large front porch, backyard fire pit, and outdoor shower. You can also walk to town, making it a convenient choice if your group wants to be close to all of the action and the wonderful things about Oak Bluffs.
Vineyard Haven
Vineyard Haven, the main village in Tisbury, has a working harbor, shops, restaurants, and convenient access to the Island’s year-round ferry service. Its location makes it a practical home base for exploring more of Martha’s Vineyard.
Featured Property 1768 Vineyard Haven
4 Bedrooms | 4.5 Bathrooms | Sleeps 8
For an upscale stay in the heart of Vineyard Haven, this four-bedroom luxury home pairs harbor views with a walkable downtown location near shops, restaurants, and the ferry. Highlights include two mahogany decks, a penthouse lounge, a gourmet kitchen, a home theater, a pool table, and a wet bar.
West Tisbury
West Tisbury offers a quieter setting with farmland, ponds, and classic New England scenery. Consider it if you want more space and a relaxed atmosphere away from the Island’s busier port communities.
Featured Property 1955 West Tisbury
5 Bedrooms | 4.5 Bathrooms | Sleeps 10
This spacious five-bedroom home offers multiple living areas, outdoor dining, and direct access to walking and biking trails. Its standout feature is a heated 15-by-30-foot private pool with chaise lounges, giving your group another way to spend a relaxing day without leaving the home.
Chilmark
Rolling hills, stone walls, rural landscapes, and the fishing village of Menemsha give Chilmark its distinctive up-Island character. It’s a good fit if you’re looking for scenery, privacy, and a slower pace.
Featured Property: 286 Chilmark
4 Bedrooms | 2.5 Bathrooms | Sleeps 8
This upscale Chilmark retreat combines classic Vineyard character with the post-and-beam architecture of an original Yankee Barn. This home features a sun-filled cathedral living room and wraparound deck for outdoor dining, with Lucy Vincent, Menemsha, and Squibnocket beaches just minutes away.
Book Your Martha’s Vineyard Rental Today!
Once you know what you want from your trip, finding where to stay in Martha’s Vineyard gets much easier.
Start with your preferred location, then consider your budget, group size, dates, and must-have amenities. From cozy Island cottages to spacious luxury properties, there are options for many ways of experiencing Martha’s Vineyard.
When you’re ready to reserve your rental home, browse available Sandcastle Realty properties, then book here. Booking directly also means working with a local Edgartown team and avoiding the additional fees charged by online travel agencies.
Book Direct and Save with Sandcastle Realty
Frequently Asked Questions
Do I need a car when staying in Martha’s Vineyard?
Not necessarily. That depends largely on where you stay and what you plan to do. Some vacation rental homes are within walking distance of town, shops, restaurants, beaches, or public transportation, while a car can be more convenient for exploring farther around the Island.
How far in advance should I book a Martha’s Vineyard vacation rental?
For popular summer dates, it’s a good idea to begin your search well in advance, especially if you need a particular location, larger home, private pool, or other specific amenities. More flexibility with dates and rental features can give you additional options.
What should I bring to a Martha’s Vineyard vacation rental?
What’s provided varies by property, so check your individual rental listing before packing. Pay particular attention to whether linens and beach towels are supplied, as well as any property-specific items or policies.
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